A Walker's Guide to Historical Trafalgar Road
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Mariners' Home - 1862 (279 Lawson Street)
Robert Wilson and his two brothers, William and George came early to Oakville. Their mother brought her ten children to Canada in 1817 from Ireland after the death of her husband.
In the 1830s, Robert was the first master of the second schooner built at Oakville, The Lady Colborne. In 1832 Robert bought a lot at the corner of Navy and King Streets. The house he built there still stands.
In the 1830s, Robert was the first master of the second schooner built at Oakville, The Lady Colborne. In 1832 Robert bought a lot at the corner of Navy and King Streets. The house he built there still stands.
He bought this property in 1837 and built the house in 1862. It became known as Mariners' Home because of his custom of bringing ill and homeless sailors to live with him. This is the same Captain Robert Wilson who helped blacks to escape across the Lake. They never failed to visit him on Emancipation Day when they gathered from this part of the province for a picnic in Oakville. He was also captain of the Baltic, built at Wellington Square in 1854, and once sailed to Liverpool with flour from the Chisholm brothers mill.
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His granddaughter provided a description of this house:
“The house was set well back from the street. A wide flower-bordered path covered at one place by a grape arbour led from the gate on Dundas Street [Trafalgar Road] up to a number of steps to the front door. This floor of the house contained a hall, parlour, sitting room and bedroom. From the sitting room, which was in the south east corner, a stairway went down into a large room right across the front half of the house. This was a combination kitchen and family dining room (the sitting room was used as a dining room on special occasions). While it was in the basement yet the windows were well above ground level. However in a very rainy season it would flood. We have recollections of the fun of running on boards from chair to chair to reach supplies in the cupboards. At the back of the room a high step took one into a hall of which were a pantry and a cellar containing bins for apples, vegetables and coal. A door in the south wall led to a short stairway up into a summer kitchen and wash house built on the side of the house.
From the front hall a long staircase went to the upstairs containing three bedrooms and a small store room. In the ceiling of the hall was a trap door reached by a ladder leading to the attic. Another trap door opened onto the roof. As some of the branches of a large cherry tree extended over the roof a picker secured by a rope could climb out on the roof through these trap doors.
The house was heated by three stoves, one each in the kitchen, sitting room and parlour. At the rear of the house was a well noted for the purity of its water. Beyond the well lay a woodhouse, then a barn which housed a cow, then a henhouse and pigsty. The northwest section of the lot was covered by an orchard, the northeast by a vegetable garden. The lot was a miniature farm. It needed to be for besides raising their own family of five, our grandparents took in four orphans and grandfather frequently brought home sick or homeless sailors in the winter. This house was truly given to dispensing hospitality, kindness and happiness. No one left without a meal or a parcel of garden produce. One of the chief social events was Capt. Robert and grandmother’s golden wedding in 1881. When the house sold the price was $1700. This was in the 1890s”
“The house was set well back from the street. A wide flower-bordered path covered at one place by a grape arbour led from the gate on Dundas Street [Trafalgar Road] up to a number of steps to the front door. This floor of the house contained a hall, parlour, sitting room and bedroom. From the sitting room, which was in the south east corner, a stairway went down into a large room right across the front half of the house. This was a combination kitchen and family dining room (the sitting room was used as a dining room on special occasions). While it was in the basement yet the windows were well above ground level. However in a very rainy season it would flood. We have recollections of the fun of running on boards from chair to chair to reach supplies in the cupboards. At the back of the room a high step took one into a hall of which were a pantry and a cellar containing bins for apples, vegetables and coal. A door in the south wall led to a short stairway up into a summer kitchen and wash house built on the side of the house.
From the front hall a long staircase went to the upstairs containing three bedrooms and a small store room. In the ceiling of the hall was a trap door reached by a ladder leading to the attic. Another trap door opened onto the roof. As some of the branches of a large cherry tree extended over the roof a picker secured by a rope could climb out on the roof through these trap doors.
The house was heated by three stoves, one each in the kitchen, sitting room and parlour. At the rear of the house was a well noted for the purity of its water. Beyond the well lay a woodhouse, then a barn which housed a cow, then a henhouse and pigsty. The northwest section of the lot was covered by an orchard, the northeast by a vegetable garden. The lot was a miniature farm. It needed to be for besides raising their own family of five, our grandparents took in four orphans and grandfather frequently brought home sick or homeless sailors in the winter. This house was truly given to dispensing hospitality, kindness and happiness. No one left without a meal or a parcel of garden produce. One of the chief social events was Capt. Robert and grandmother’s golden wedding in 1881. When the house sold the price was $1700. This was in the 1890s”
The Samuel Lawson House - 1837 (280 Lawson Ave)
It's likely that Samuel Lawson and his family were the first to settle so far north of the village proper, as no other houses existed between theirs and Potter's at Sheddon Street (now Freestone Lane) at the time (1837). Wanting to build a house for his family but unable to finance the purchase of both land and a house1, he obtained from William Chisholm title to park lot K, for which he was to pay when he could. He built a one-and-a-half storey house of hand-made brick (the first in Oakville) on the property, facing Trafalgar Road and surrounded by an apple orchard. Over time the street bordering the property on the north became known as Lawson Street.
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323 Trafalgar Road

The background to this home is in the research stage. If you have information you'd care to share, we'd LOVE to hear from you!
331 Trafalgar Road
The background to this home is in the research stage. If you have information you'd care to share, we'd LOVE to hear from you!
In 2008 a sign was attached to the building: "1893 - William C. Gailbrath - Carpenter |
Kerosene Castle - c1856 (337 Trafalgar Road)
This house, Kerosene Castle, was built about 1856 by Richard Shaw Wood, owner of The Oakville Oil Refinery which stood across the street. The refinery produced kerosene or coal oil – hence the name – and was one of the largest in Canada.
Wood, who came to Oakville from Bermuda in the late 1850s was essentially a promoter and a man of many parts. He habitually wore a fur hat even in the summer to show his affluence rather than because of the climate. |
In 1866 the refinery burned down, as chronicled in this 13 July 1866 report in the Hamilton Spectator entitled Great Fire At Oakville. Burning oil floated downstream as far as the harbour. The fire was caused by a defect in a new very large still which had recently been installed. The fire burned all day and destroyed four other stills, the storage tanks and several wooden buildings. The refined oil was saved. No attempt was made to rebuild and for years the river bank was strewn with debris. Until quite recently oil was still seeping up into the marsh at the foot of the hill.
The house was a single family residence until the mid 1900s when it was split to become a nursing home on one side and apartments on the other. In 1978 it started its transformation into MacLachlan College, a private day school.
The building is in a style called Second Empire which came to Canada from France in the mid to late 1800s during the Second Empire of Napoleon III. The style was very popular for public buildings for a short time. For smaller buildings and houses the style is less elaborate but is still ornate and features high windows with elegant mouldings. The typical mansard roof with gabled or elliptical dormers. This building features an oriel window on the front of the tower.
In 1867 Shaw also built the brick house at the corner of Navy and Robinson Streets and built a two-storey addition on the back which was supposed to have been for a bank.
He also owned a planing mill which stood across the street but south of Lawson Street. The mill was built by Thompson Smith in 1856 and was powered by a steam boiler. The site was chosen because of fresh water springs east of Reynolds Street. The water was piped from there to feed the boiler. The mill produced flooring, shingles, window sashes, doors, blinds etc.
When Smith moved to Toronto, Shaw bought the mill and in the late 1860s started making Superior Brand washing machines. The mill was bought from Wood’s widow in 1887 by James McDonald Jr and burned two years later. It was rebuilt and became the site of Oakville’s first electricity generator in 1892 but it was found that the wood-fired boilers wouldn’t do the job. It burned again in 1893 and wasn’t rebuilt.
Captain Francis Brown’s house across the street from the mill / electricity generator was seriously endangered but didn’t burn. The two black walnut trees currently flanking the entrance walk sprouted from the stumps of those killed by that 1893 fire.
The stack for the boilers remained for many years until demolished by dynamite in 1911.
A little further north on the creek bank north of Division Street, now MacDonald Road, was a steam brewery owned in 1858 by James Brown. In 1863 it was taken over by Henry Hogben and when Francis J. Brown bought it about 1870, he changed the name to Victoria Brewery after which it promptly went out of business. Division Street runs on the line separating the north from the south half of lot 13, concession 3 South of Dundas Street. It formed the northern boundary of the village, separating it from the wilderness.
The house was a single family residence until the mid 1900s when it was split to become a nursing home on one side and apartments on the other. In 1978 it started its transformation into MacLachlan College, a private day school.
The building is in a style called Second Empire which came to Canada from France in the mid to late 1800s during the Second Empire of Napoleon III. The style was very popular for public buildings for a short time. For smaller buildings and houses the style is less elaborate but is still ornate and features high windows with elegant mouldings. The typical mansard roof with gabled or elliptical dormers. This building features an oriel window on the front of the tower.
In 1867 Shaw also built the brick house at the corner of Navy and Robinson Streets and built a two-storey addition on the back which was supposed to have been for a bank.
He also owned a planing mill which stood across the street but south of Lawson Street. The mill was built by Thompson Smith in 1856 and was powered by a steam boiler. The site was chosen because of fresh water springs east of Reynolds Street. The water was piped from there to feed the boiler. The mill produced flooring, shingles, window sashes, doors, blinds etc.
When Smith moved to Toronto, Shaw bought the mill and in the late 1860s started making Superior Brand washing machines. The mill was bought from Wood’s widow in 1887 by James McDonald Jr and burned two years later. It was rebuilt and became the site of Oakville’s first electricity generator in 1892 but it was found that the wood-fired boilers wouldn’t do the job. It burned again in 1893 and wasn’t rebuilt.
Captain Francis Brown’s house across the street from the mill / electricity generator was seriously endangered but didn’t burn. The two black walnut trees currently flanking the entrance walk sprouted from the stumps of those killed by that 1893 fire.
The stack for the boilers remained for many years until demolished by dynamite in 1911.
A little further north on the creek bank north of Division Street, now MacDonald Road, was a steam brewery owned in 1858 by James Brown. In 1863 it was taken over by Henry Hogben and when Francis J. Brown bought it about 1870, he changed the name to Victoria Brewery after which it promptly went out of business. Division Street runs on the line separating the north from the south half of lot 13, concession 3 South of Dundas Street. It formed the northern boundary of the village, separating it from the wilderness.
William Bigger Chisholm House - c1881 (385 Trafalgar Road)

This house was built in 1881 by William Bigger Chisholm, a grandson of the founder of the town. He was a brother of Charles Pettit Chisholm whose home we saw down the street. He and his brother bought the Victoria Brewery (across the street from 385 Trafalgar) from Francis J. Brown (whose house we saw earlier) in 1874 – it had been idle for four years – and turned it into a basket factory for the strawberry business.
The basket factory was an important business in town. In 1877 nearly three quarters of a million baskets were manufactured. There were piles of logs up and down Trafalgar and there were many complaints about the road being blocked. The opinion on Town Council was that if the log piles were necessary to an industry which afforded the town great benefits, the inconvenience they caused was incidental. When the basket factory started up, W.B. Chisholm lived in a house on the north east corner of Reynolds and MacDonald Road – we’ll pass it later. He moved his family here in 1881 and died in 1889.
The basket factory was an important business in town. In 1877 nearly three quarters of a million baskets were manufactured. There were piles of logs up and down Trafalgar and there were many complaints about the road being blocked. The opinion on Town Council was that if the log piles were necessary to an industry which afforded the town great benefits, the inconvenience they caused was incidental. When the basket factory started up, W.B. Chisholm lived in a house on the north east corner of Reynolds and MacDonald Road – we’ll pass it later. He moved his family here in 1881 and died in 1889.
The following year the basket factory was taken over by Pharis Doty and Son and in 1892 The Oakville Basket Company, a joint-stock venture, was formed. On 29 April 1893 the entire factory burned by arson. Suspicion centred on Robert McKenzie Chisholm, another brother of C.P. and W.B. Chisholm. He had been confined in the Toronto Asylum because of mental illness but had recently been released. When interviewed by Chief Sumner, he readily confessed and was returned to the asylum where he died soon after.
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It burned again in 1919 after which it moved to the west side of Trafalgar Road, between Cornwall Road and the railway. “The Basket”, as it was called, used boiling water to loosen the bark on the logs before large sheets of veneer were peeled off like paper towels off a roll. Berry boxes were made of basswood as it didn’t taint the fruit. Other baskets were made of any hardwood with a softwood bottom. Over the years several employees fell to their deaths in the vat of boiling water. Power to run the factory was provided by a steam engine fueled by wood chips and bark. The steam whistle could be heard all over town when it called the employees to work and sounded
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for lunch and the end of the work day. The steam whistle also served to call the volunteer fire department. A code was set up to tell them the approximate location of the fire. The basket factory closed for good and was demolished in 1988. All that is left of it now is the steam engine which was moved a few years ago to the south side of Cornwall Road at the brow of the hill. (For a little more about the breweries and basket factory, click here.)
The house is a blend of several styles of Victorian architecture. The Classic Revival style is shown in the medium pitched roof, centre gable of the north façade and the ogee-shaped medallions in the gables. The Italianate style is evident at the main entrance with its intricate leaded glass, double doorway with full length transom and side panels with flush lights.
1 Mathews, Hazel C., Oakville and the Sixteen: The History of an Ontario Port (Toronto: University of Toronto Press, 1971). Pg. 53-54.